Benzylamine → HCID 49765219, compound

HRID 273270Notes

Reaction equation

HRID 273270 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([NH:16][C@@H:17]([CH2:24][C@H:25]([CH3:32])[CH2:26]OS(C)(=O)=O)[CH2:18]OS(C)(=O)=O)=[O:15])([CH3:12])([CH3:11])[CH3:10]>COCCOC>[C:9]([O:13][C:14](=[O:15])[NH:16][C@H:17]1[CH2:24][C@H:25]([CH3:32])[CH2:26][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:18]1)([CH3:10])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 60004301HCID 60004301, compound

Product 1

HCID 49765219HCID 49765219, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A 50 L reactor is charged with 9.1 Kg of neat benzylamine. The reactor is brought to 55° C. and a solution of intermediate (6) (8.2 Kg) in 1,2-dimethoxyethane (DME) (14.1 Kg) is added to the reactor while maintaining a temperature of 60° C.±5° C. After complete addition of this solution, the reaction is stirred at 60° C.±5° C. for several hours and monitored for completion by TLC or HPLC. The reaction is cooled to ambient temperature and volatiles (DME) are removed by rotary evaporation under vacuum. The residue is diluted with 11.7 Kg of 15% (v/v) ethyl acetate/hexanes solution and treated, while agitating, with 18.7 Kg of 20% (wt) aqueous potassium carbonate solution. A triphasic mixture is obtained upon settling. The bottom aqueous phase is removed and the middle phase is set aside. The upper organic phase is collected and held for combination with extracts from additional extractions. The isolated middle phase is extracted twice again with 11.7 Kg portions of 15% (v/v) ethyl acetate/hexanes solution, each time combining the extracts with original organic phase. The combined organic extracts are transferred into a rotary evaporator and solvent is removed under vacuum until an oily residue remains. The residue is then purified via large-scale preparative chromatography to afford purified intermediate (7) as an oil.

Workup

  1. customis brought to 55° C.
  2. temperaturewhile maintaining a temperature of 60° C.±5° C
  3. additionAfter complete addition of this solution
  4. customvolatiles (DME) are removed by rotary evaporation under vacuum
  5. additionThe residue is diluted with 11.7 Kg of 15% (v/v) ethyl acetate/hexanes solution
  6. additiontreated
  7. stirringwhile agitating, with 18.7 Kg of 20% (wt) aqueous potassium carbonate solution
  8. customA triphasic mixture is obtained
  9. customThe bottom aqueous phase is removed
  10. customThe upper organic phase is collected
  11. extractionheld for combination with extracts from additional extractions
  12. extractionThe isolated middle phase is extracted twice again with 11.7 Kg portions of 15% (v/v) ethyl acetate/hexanes solution
  13. customThe combined organic extracts are transferred into a rotary evaporator and solvent
  14. customis removed under vacuum until an oily residue
  15. customThe residue is then purified via large-scale preparative chromatography
  16. customto afford
  17. custompurified intermediate (7) as an oil

Sources & evidence

ORD record
ord-9464f890227048eabcf81cd477eb87de
Source dataset
uspto-grants-2008_11
Patent number
US07456279B2

Reaction notes

Loading…